Synthesis of 4-alkyl-4-alkoxybutenolides having unsaturated side chains via chromium carbene complex photochemistry:(+)-cerulenin

TE Kedar, MW Miller, LS Hegedus

Index: Kedar, Tracey E.; Miller, Michael W.; Hegedus, Louis S. Journal of Organic Chemistry, 1996 , vol. 61, # 18 p. 6121 - 6126

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Citation Number: 34

Abstract

The photochemical reaction between optically active ene carbamates and chromium alkoxycarbene complexes containing unsaturated aliphatic side chains was further developed. Although remote olefinic groups, including conjugated dienes, were tolerated, a homoallylic side chain underwent intramolecular reaction to give a strained cyclobutanone.(+)-Cerulenin was synthesized utilizing the photochemical reaction of an ...